Piancastagnaio Holiday Rentals

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Our top choices for Piancastagnaio holiday rentals

Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi

Siena
10.0 out of 10, Exceptional, (1)
"Bellissime camere, dotate di ogni confort, immerse nel verde della campagna toscana. Camere spaziose, comode, luminose e attrezzate di tutto. Proprietari ospitali e gentili, sempre pronti a fornire indicazioni. Grazie di tutto , torneremo senz'altro!"
United States
Annarosa m.
Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi

Hotel San Gregorio

3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is NZ$399
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Siena
9.4 out of 10, Exceptional, (67)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
United Kingdom
peter H.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Casanova - Panoramic Rooms and Suites

3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is NZ$367
includes taxes & fees
11 Dec - 12 Dec
Casanova - Panoramic Rooms and Suites

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

chiusi
10.0 out of 10, Exceptional, (57)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

The House of Alice, charm and relaxation

Montalcino (SI)
9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is NZ$435
includes taxes & fees
15 Dec - 16 Dec
The House of Alice, charm and relaxation

Bellarmino Boutique Apartments

Montepulciano
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is NZ$210
includes taxes & fees
11 Dec - 12 Dec
Bellarmino Boutique Apartments

Residenza Fabroni

Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is NZ$178
includes taxes & fees
11 Dec - 12 Dec
Residenza Fabroni

Villaggio Le Querce

4.0 star property
Sorano
9.0 out of 10, Wonderful, (57)
"Nice neighborhood with Sorano close by. No restaurant or bar open. Lack of bedsheets and towels for 3 people. The shower head was too heavy to stay in the shower head holder"
Finland
Åsa
The price is NZ$188
includes taxes & fees
24 Dec - 25 Dec
Villaggio Le Querce

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (114)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is NZ$508
includes taxes & fees
15 Dec - 16 Dec
Il Tosco

Country House With Private Pool

Toscane
10.0 out of 10, Exceptional, (13)
"We had such a lovely week staying in this farmhouse just outside Citta della Pieve. The house itself and interiors are beautiful - the kitchen is well equipped, the beds are incredibly comfortable, the bathrooms modern, the pool is an excellent size, and the views are amazing. The hosts were incredibly friendly and generous, and really added to our overall experience. I would highly recommend a stay here - you will not be disappointed!"
United Kingdom
Clare C.
Country House With Private Pool

Osteria del Borgo

Montepulciano
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo

Villa Casale Silvia Large Private Pool, A/C, WiFi

Parrano
9.4 out of 10, Exceptional, (22)
"A lovely escape - we enjoyed every moment!"
United States
Anonymous traveller
Villa Casale Silvia Large Private Pool, A/C, WiFi

Eco house with pool and fantastic views

Scansano
8.6 out of 10, Excellent, (7)
"Ci siamo trovati molto bene in questa struttura, spaziosa, ed accogliente. Abbiamo usata anche la piscina perfetta"
Italy
Marco S.
Eco house with pool and fantastic views

Villa with private pool, air conditioning near wineries at 3km from village

CHIANCIANO terme
9.4 out of 10, Exceptional, (46)
"It was amazing!! Great space for 7 adults. Pool area is great. Definitely do a meal with Leonardo. "
United States
Carol W.
Villa with private pool, air conditioning near wineries at 3km from village

Tuscany romance. Rural charm between Montalcino and sea. Relax pur

Cinigiano
9.6 out of 10, Exceptional, (40)
"Very Clean and excellent House. We loved our stay. "
Germany
Sebastian K.
Tuscany romance. Rural charm between Montalcino and sea. Relax pur

FARM SANT'ANTONIO / CHARMING VILLA WITH PRIVATE BEACH

Bolsena
9.6 out of 10, Exceptional, (4)
"The setting is just gorgeous - gardens, vegetation and the building exterior. Very spacious well-kept grounds with access (via a steep path) to the lake-side and the peaceful and secluded private beach. Lovely pool area and decent-sized well-maintained pool. The apartment interior was spacious and rustic - fairly basic but authentic farmhouse furnishings. The only negative thing to say would be that it could have been cleaner."
United Kingdom
Mairi C.
FARM SANT'ANTONIO / CHARMING VILLA WITH PRIVATE BEACH

Villa Piandisette - Four Bedroom Villa, Sleeps 10

Cetona
9.4 out of 10, Exceptional, (11)
"Very nice property, clean and chic, all the furniture and amenities you need. Very big and specious. In summer can be very hot but the villa has Airconditioning in every room. Owner very nice and helpful, we communicated via WhatsUp for everything. The closest supermarket is 10 min drive away so plan your shopping well. "
Austria
Ana J.
Villa Piandisette - Four Bedroom Villa, Sleeps 10

Charming House in the heart of Montepulciano

Montepulciano
9.8 out of 10, Exceptional, (65)
"Location, location, location. The room was great. The host was easy to communicate with and was very helpful."
United States
peter m.
Charming House in the heart of Montepulciano

Delcorto Suites

Montepulciano
10.0 out of 10, Exceptional, (32)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is NZ$346
includes taxes & fees
11 Dec - 12 Dec
Delcorto Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Piancastagnaio Hotel Reviews

Find out more about Piancastagnaio

Everything you need to know about Piancastagnaio holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Piancastagnaio holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Piancastagnaio holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Piancastagnaio holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Piancastagnaio. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Piancastagnaio holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Piancastagnaio holiday rentals we have selected for you start as low as NZ$178 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Piancastagnaio rentals

At Expedia, we put the best Piancastagnaio holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Piancastagnaio rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Piancastagnaio holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Piancastagnaio. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Piancastagnaio?

Yes, there are holiday rentals close to the most popular sights in Piancastagnaio, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Piancastagnaio has to offer?

The House of Alice, charm and relaxation: This holiday home rental outside of Piancastagnaio is located in a rural location, and has a fireplace, a terrace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals will I find in Piancastagnaio?

Choose from 4 Expedia holiday rentals in Piancastagnaio for a memorable holiday.

What’s there to see and do in Piancastagnaio?

Explore the area and family-friendly sights such as Villa Acquaviva - La Fattoria, or get out into nature at a spot like Terme di Saturnia. In the wider area, you’ll find Abbazia di San Salvatore and Monte Amiata.

What’s a holiday rental in Piancastagnaio like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Piancastagnaio. Holiday rentals offer extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for families.